Operations AI Lead, Trilogy (Remote) - $200,000/year USD at Crossover, London, £Contract Rate

This is not a traditional VP-level position. You will not oversee a team, attend recurring status meetings, or develop quarterly strategy presentations. There are no steady-state operations to maintain.

Your responsibilities will include leading M&A diligence and integration processes for enterprise software businesses, managing P&L objectives for business units, developing AI-powered automations with cutting-edge tooling, negotiating contracts with vendors, and delivering presentations to portfolio CEOs, CFOs, and functional leaders. All of this work you will execute independently and simultaneously across multiple organizations.

Trilogy specializes in acquiring distressed enterprise software businesses and executing turnarounds, targeting one acquisition weekly. Our 10-person VP of Operations team operates across more than 50 portfolio companies. The work encompasses three core areas: complete acquisition cycles from diligence through integration, serving as effective COO for business units (including budget management, P&L oversight, and vendor relations), and providing consulting support to central functions (Support, SaaS, Engineering) to align their initiatives with business results.

This high-stakes, high-visibility position offers no typical workday. You will shape decisions involving key stakeholders throughout the organization—portfolio CEOs, functional leaders, and deal-side collaborators. Success in this role requires building conviction independently, assembling supporting evidence, and driving stakeholders to action without waiting for consensus.

What You Will Be Doing

• Leading M&A due diligence in partnership with top-tier investment banks and financial institutions, organizing VDR frameworks, executing vendor consolidation initiatives, coordinating international payroll migrations, and managing closing task lists
• Managing quarterly P&L budgets for multi-product business units, uncovering margin optimization opportunities, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance executives
• Applying AI tools (Claude Code, Cursor, and the most effective alternatives available) on a daily basis to examine vendor expenditure, automate decision workflows, construct cost projection models, and generate executive-level reports without assistance
• Overseeing the complete vendor management lifecycle spanning 70+ contracts, encompassing negotiation, legal assessment, procurement processes, invoice management, and contract termination
• Serving as the single integration point for portfolio operations, coordinating among 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side collaborators (banking institutions, legal advisors, target company C-Suite)
  
  

What You Won’t Be Doing

• Leading a team or assigning tasks to subordinates. You execute the work directly.
• Developing strategy presentations or conceptual frameworks. Every deliverable is tied to financial impact.
• Participating in status update meetings or reporting on KPIs. You are accountable for the KPIs.
• Waiting for direction on next steps. You pinpoint the issue, create the solution, and implement it.
• Focusing on a single initiative. You will manage 3-5 parallel workstreams across separate companies.
  
  

Basic Requirements

Operations AI Lead key responsibilities

• 5+ years of operational leadership in business operations
• Experience making presentations to C-suite executives
• Experience writing automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
• Remote work capability with at least 6 hours of overlap with the CST time zone
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5145-GB-London-OperationsAILe.003